Co-created by Dave Chappelle and Neal Brennan, “Chappelle’s Show” was an American sketch comedy series that deftly skewered intricate cultural topics such as race, sex, drugs, gun violence, prostitution, and the entertainment industry. His 2004 sketch about Rick James, arguably the first TV comedy sketch ever to go viral, gifted the world with the, for-some-time-inescapable, catchphrase “I’m Rick James!” Chappelle walked away from the show at the height of its success, which only added to its already legendary status.
Here are a few things you might not know about the show that showed us the real Wayne Brady.
26. The Audience Was Probably Just Dumb
The sketches were usually prerecorded and audience reaction was used in lieu of a laugh track. The only time a laugh track was used was in the sketch, “Dude’s Night Out,” which failed to garner the audible audience reaction they wanted.
The original theme song was supposed to have lyrics, but the band couldn’t sync the lyrics to the music so Chappelle instructed the two musicians to just keep saying “Chappelle’s Show” over and over again.
24. Is There Nothing Boobs Can’t Do?
Hugh Hefner has inspired many things and, apparently, “Chappelle’s Show” is one of them. Chappelle was watching a special on Hefner in which musicians and comedians performed for The Hef and his Playboy Bunnies. On “Inside the Actors Studio,” Chappelle said he was “weirdly inspired” by this, called up his co-creator Neal Brennan, and the ensuing conversation led to the creation “Chappelle’s Show”.
Chappelle and Brennan initially brought the show to HBO and they passed on it. Because they’re dumb.
22. Super Successful Sketch Writing for Dummies
Chappelle and Brennan claim that they learned how to write the show by reading the book “Live From New York: The Complete, Uncensored History of Saturday Night Live as Told by Its Stars, Writers, and Guests.” Good thing they didn’t read American Psycho or the show might have turned out real different.
21. He’s Still Offended
Wayne Brady was reportedly unhappy when Negrodamus dissed him, saying “White people love Wayne Brady, because Wayne Brady makes Bryant Gumbel look like Malcolm X.” At the NAACP Image Awards, Brady bought some of the Chappelle Show crew drinks and brought up his feelings about that sketch. The next day, Chappelle called him up and the famous sketch showing off Brady’s dark side was born. And he didn’t even have to choke anyone.
20. He Made It All Up
Paul Mooney, who played black prophet in one skit, used to be a writer for Richard Pryor and ad-libbed many of his responses on the Chappelle’s Show, including the one that upset Wayne Brady.
19. Good Help is Hard to Find
Chappelle wasn’t originally planning on playing Samuel L. Jackson in the fake beer commercial but everyone they hired to do it failed to live up to Chappelle’s expectations. So he just did it himself.
Chappelle playing Samuel L. Jackson
18. Ninety-Nine Problems and the RZA is One
The Racial Draft sketch was filmed right across the street from Jay-Z’s “final” concert. During the shoot, the RZA disappeared for an hour, delaying production. He returned and explained that he had wandered over to Madison Square Garden to watch the concert.
17. Whuuuut?! Yeeeeah! Okaaayyy!
Apparently, Dave Chappelle made Lil Jon. “This Dave Chappelle skit just really put me on a different level,” the hip-hop artist told MTV. “He basically thrusted me into pop culture, and not just urban, but white society as well. I was in the airport, like, three weeks ago, and this 60 year old white lady came up to me and was like ‘Aren’t you Lil Jon?’” Because in hip-hop, being recognized by old white ladies is how you know you’ve made it. Just ask the Sugarhill Gang.
16. From One Genius to Another
After Chappelle and Charlie Murphy showed Eddie Murphy the Rick James sketch, Eddie watched it in complete silence. When it ended, he told them it was “genius” before laughing that Eddie Murphy laugh (you know exactly what we mean) and insisting they play it for him again.
15. Politics is a pain
The famous Rick James sketch caused quite a few problems for a politician also named Rick James who was running for city council in Hattiesburg, Mississippi. His campaign signs were either stolen or defaced by people who added the jokes from the Chappelle show.
After the Prince sketch came out, the singer/songwriter confirmed that he did indeed beat Charlie Murphy at basketball, however, he contended that it wasn’t because he was good, but that Charlie Murphy was bad.
13. Game, Blouses
In 2013, Prince released his single “Breakfast Can Wait” using a picture of Chappelle dressed as him on the cover. About the cover Chappelle mused, “That’s a Prince Judo move right there. You make fun of Prince in a sketch and he’ll just use you in his album cover. What am I going to do – sue him for using a picture of me dressed up like him? That’s checkmate right there.”
12. His Prerogative
Bobby Brown was supposed to appear in the “STD Sesame Street” sketch, but got arrested before he could. He was replaced by Snoop Dogg who was just responsible enough not to get arrested on the day of the shoot.
11. He’s Not Wrong
When fans kept yelling “I’m Rick James!” during one of Chappelle’s stand-up shows, he infamously walked off the stage in anger. When he returned, he had this to say: “You know why my show is good? Because the network officials say you’re not smart enough to get what I’m doing, and every day I fight for you. I tell them how smart you are. Turns out, I was wrong. You people are stupid.”
10. Right Schurrrr
Before partnering with Dave, “Chappelle’s Show” co-creator Neal Brennan was partnered with Mike Schur, and together they wrote a number of scripts that never got produced including a movie called “The Oldest Man in the World,” about a museum dedicated to the oldest man in the world. Schur went on to create “Parks and Recreation,” “Brooklyn Nine Nine,” and “The Good Place.”
9. Foot in the Door
Brennan got his start working the door at the Boston Comedy Club. He would write jokes for the comedians he saw on stage, and eventually, they started to pay him for his writing. “Chappelle always said when I gave him a punchline that it was super annoying,” Brennan recalls, “but still, with the first one, he was like, Hmm, he’s right.”
8. Long Overdue
Although he would famously walk away from it later, at the time, the deal that Chappelle struck with Comedy Central for two more season of Chappelle’s Show was one of the most lucrative in television history paying him a hefty salary in addition to a significant percentage of future DVD sales. “The deal made it very hard for me to say no,” Chappelle said, “I’m not sure, but I believe there is a clause that gives me reparations for slavery.”
7. Et tu Charlie Murphy? Et tu?
When Chappelle left the show early on in the third season, they had filmed enough material to put together three episodes. In place of Chappelle, Charlie Murphy and Donnell Rawlings hosted the live studio audience segments.
6. This is Why We Can’t Have Nice Things
The sketch that killed “Chappelle’s Show” was about a black pixie, played by Chappelle, who wore blackface and tried to convince black people to act in stereotypical ways. It was the sort of joke that Chappelle and his friends would laugh about. However, at the taping, a white audience member laughed particularly loudly and it made Chappelle uncomfortable. Chappelle then wondered if his show had gone from subverting stereotypes to reinforcing them and promptly quit.
5. So You’re Saying There’s a Chance
In 2006, Chappelle said that he would be open to producing the remainder of Season 3, and perhaps even a Season 4, but only if his demands were met, one of which was to ensure that half the proceeds from future DVD sales would be donated to charity.
4. Who’s My Daddy?
Some of the sketches shot for the aborted third season but never made it to air were: A parody of Michael Jackson videos referencing his child molestation trial, a parody of “Super Size Me” called Maximize Me, and a sequel to Daddy Day Care staring Charlie Murphy. The first two might be a little outdated but Daddy Day Care 2 would be amazing.
3. Funny Money
Barry Katz, Chappelle’s former agent, recounts a story where Doug Herzog, president of Comedy Central demanded that Katz get Chappelle into his office so he could give him a cheque for US $27 million as part of his payment to do a third season of Chappelle’s Show. Katz told Herzog that he wouldn’t be able to do it and Herzog, enraged, hung up on him screaming, “Twenty seven million dollars!” Later on, Katz recounted the story to Chappelle, emphasizing the amount that Herzog had quoted, and Chappelle, with his perfect comic timing, leaned forward and said, “That sounds a little light.”
2. Live From New York
The Saturday Night Live episode that Chappelle hosted in 2016, which included a sketch where Chappelle brought back all his “Chappelle’s Show” characters in a spoof on the Walking Dead, was the highest rated episode since 2013.
Speaking about Chappelle’s Show in 2014, Dave Chappelle said, “Technically, I never quit. I’m seven years late for work.”